Methanol → 1-[(4-Methoxynaphth-1-yl)methyl]piperidine

HRID 1609818Notes

Reaction equation

HRID 1609818 reaction equation
N1(C2C=CC(O[CH:11]3[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)=CC=2)C=CN=C1.CO.[CH3:21][O:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH:33]=O)=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:21][O:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH2:33][N:13]2[CH2:14][CH2:15][CH2:16][CH2:11][CH2:12]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 852174-Methoxy-1-naphthaldehydeHCID 222600603-[4-(Imidazol-1-yl)phenoxy]piperidine

Product 1

HCID 7832201-[(4-Methoxynaphth-1-yl)methyl]piperidineYield 16.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[4-(imidazol-1-yl)phenoxy]piperidine (308 mg, 1.26 mmol), methanol (6.0 mL) was added 4-methoxy-1-naphthaldehyde (1.25 eq, 298 mg), followed by borane pyridine complex (0.196 mL, 1.25 eq.). The resulting mixture was stirred overnight. The methanol was evaporated, and the residue diluted with ethyl acetate, washed with water and brine. Evaporation of the solvent in vacuo gave a crude product. Flash column chromatography on silical gel with 1-2% methanol in methylene chloride afforded 3-[4-(imidazol-1-yl)phenoxy]-]-1-[(4-methoxynaphth-1-yl)methyl]piperidine (54 mg), 1H NMR(CDCl3) 8.30 (m, 2), 7.70 (s, 1), 7.50 (m, 2), 7.30 (s, 1), 7.20 (m, 4), 6.90 (m, 2), 6.70 (d, 2), 4.30 (m, 1), 4.00 (s, 3), 3.90 (AB q , 2), 3.10 (m, 1), 2.80 (m, 1), 2.10-2.30 (m, 3), 1.80 (m, 1), 1.40-1.70 (m, 2) ppm.

Workup

  1. customThe methanol was evaporated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with water and brine
  4. customEvaporation of the solvent in vacuo
  5. customgave a crude product

Sources & evidence

ORD record
ord-4235e5392d254386b3078ed80cfb07a3
Source dataset
uspto-grants-2006_01
Patent number
US06982259B2

Reaction notes

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